m-Anisidine

Base Information

• Chemical Name: m-Anisidine
• CAS No.: 536-90-3
• Deprecated CAS: 918666-97-4
• Molecular Formula: C7H9NO
• Molecular Weight: 123.155
• Hs Code.: 29222200
• European Community (EC) Number: 208-651-4
• ICSC Number: 0375
• NSC Number: 7631
• UN Number: 2431
• UNII: JXA144KX2I
• DSSTox Substance ID: DTXSID8024529
• Nikkaji Number: J1.593H
• Wikipedia: M-Anisidine
• Wikidata: Q3296585
• Metabolomics Workbench ID: 123558
• ChEMBL ID: CHEMBL1500995
• Mol file: 536-90-3.mol

Synonyms:3-anisidine;m-anisidine

Chemical Property of m-Anisidine

Chemical Property:

• Appearance/Colour: Pale yellow oily liquid or dark red liquid
• Vapor Pressure: 0.0209mmHg at 25°C
• Melting Point: ?1-1 °C(lit.)
• Refractive Index: n20/D 1.581(lit.)
• Boiling Point: 251 °C at 760 mmHg
• PKA: 4.23(at 25℃)
• Flash Point: 109.6 °C
• PSA: 35.25000
• Density: 1.064 g/cm³
• LogP: 1.85860
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: 18g/l
• Water Solubility.: <0.1 g/100 mL at 19℃
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 123.068413911
• Heavy Atom Count: 9
• Complexity: 85
• Transport DOT Label: Poison

Purity/Quality:

99%min ^*data from raw suppliers

m-Anisidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+, N, Xn
• Hazard Codes: Xn,N,T+
• Statements: 22-36/37/38-50/53-51/53-33-26/27/28
• Safety Statements: 26-60-61-45-36/37-28B

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aromatic
• Canonical SMILES: COC1=CC=CC(=C1)N
• Recent EU Clinical Trials: A Phase 2, Single-Arm Study to Evaluate the Safety and Pharmacokinetics of Alefacept in Adolescent Subjects with Moderate to Severe Psoriasis
• Inhalation Risk: A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance may cause effects on the blood. This may result in the formation of methaemoglobin. Medical observation is indicated. The effects may be delayed.
• Uses: m-Anisidine is a highly poisonous monosubstituted aniline used as corrosion inhibitorsfor aluminum, copper and other metals in acidic solutions. The unusually large amount of dibromo product produced upon bromination of m-anisidine may be attributed to the two doubly activeated positions. The best enantioselectivity of 97 % ee was observed for the reaction of m-anisidine in organocatalytic asymmetric three-component cyclization of cinnamaldehydes and primary amines with 1, 3-Dicarbonyl Compounds. Evidence for the control of 2nd-harmonic generation activities from the x-ray crystal-structures of the complexes of l-tartaric acid with m-anisidine and p-toluidine was determined.

Technology Process of m-Anisidine

There total 105 articles about m-Anisidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

3-methoxyphenyl bromide (2398-37-0) → m-Anisidine (536-90-3,918666-97-4)

Guidance literature:

With bis(tri-ortho-tolylphosphine)palladium⁽⁰⁾; (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; ammonia; sodium t-butanolate; In 1,4-dioxane; at 80 ℃; for 5h; Inert atmosphere;

DOI:10.1021/ja903049z

Reference yield: 99.0%

1-chloro-3-methoxy-benzene (2845-89-8) → m-Anisidine (536-90-3,918666-97-4)

Guidance literature:

With bis(tri-ortho-tolylphosphine)palladium⁽⁰⁾; (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; ammonia; sodium t-butanolate; In 1,4-dioxane; at 100 ℃; for 12h; Inert atmosphere;

DOI:10.1021/ja903049z

Reference yield: 99.0%

carbonic acid dimethyl ester (616-38-6) + m-Hydroxyaniline (591-27-5) → m-Anisidine (536-90-3,918666-97-4)

Guidance literature:

With dimanganese decacarbonyl; at 180 ℃; for 1h;

DOI:10.1134/S1070428015030070

upstream raw materials:

3-nitroanisole

2-Chloroanisole

phenylsulfonyl azide

methoxybenzene

Downstream raw materials:

1-(3-methoxyphenyl)pyrrolidin-2-one

2-(3-methoxyphenyl)-1H-isoindole-1,3(2H)-dione

3-furan-2-yl-N-(3-methoxy-phenyl)-3-oxo-propionamide

N-(2-m-anisidino-ethyl)-phthalimide

Refernces

• 1、 Zhang, Chang-Rui,Wang, Yu-Lu,Wang, Jin-Ye. "Reduction of aromatic nitro compounds under solvent-free conditions using alumina-supported hydrazine/FeNH4(SO4)2· 12H2O". . p. 569 - 570. Retrieved 2004.
• 2、 Bordet, Alexis,Goclik, Lisa,Leitner, Walter,Walschus, Henrik. "Selective hydrodeoxygenation of acetophenone derivatives using a Fe25Ru75@SILP catalyst: a practical approach to the synthesis of alkyl phenols and anilines". supporting information. p. 2937 - 2945. Retrieved 2022/04/07.
• 3、 Sadeghi, Samira,Karimi, Meghdad,Radfar, Iman,Gavinehroudi, Reza Ghahremani,Saberi, Dariush,Heydari, Akbar. "Efficient strategy for interchangeable roles in a green and sustainable redox catalytic system: IL/PdII-decorated SBA-15 as a mesoporous nanocatalyst". . p. 6682 - 6692. Retrieved 2021/04/22.